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The quintessential small New England town of Chester is located in Rockingham County and is home to approximately 4,625 people. Incorporated in 1722, it may have been the first of the settlement grants by Massachusetts selected for expansion of growing populations in the seacoast.


According to recent figures, Chester has approximately the third highest median property values in the state, and residents have one of the highest median incomes. It is nestled 49 miles north of Boston and a short drive to the state’s largest city of Manchester or nearby Derry while offering residents the small town feel complete with farms and apple orchards.


The town has a total area of 26 square miles and is a short drive to Manchester-Boston Regional Airport or less than an hours drive to Boston’s Logan airport, which means convenient air travel to most any location in the US and Canada. Interstate 93 and 495 is the major nearby highways connecting the town to points north and south. Route 125 and 101 connects the town to the Seacoast.

Wason Pond Conservation and Recreation Area is a former Campground turned public where residents can go to enjoy a quiet, natural place to walk, hike, cross country ski, walk dogs, horseback ride, canoe, kayak, picnic, and swim.

The Chester school system consists of elementary and middle school students attending Chester Academy (public), and the High School is a contracted attendance with Pinkerton Academy, in Derry (privately operated, but it contracts with Derry, Chester, and Hampstead. Those three towns pay the academy with tax money.)


SCARECROWS: There is one town in New Hampshire where pretty much everyone gets into the Halloween spirit every October. If you happen to be in the small town of Chester and you run into a scarecrow, don’t be alarmed, there are hundreds of them scattered around. The town has been going scarecrow crazy for 5 years, making over 100 per year. That means there are more than 500 scarecrows now. In reality it is a fundraising project for the Chester historical society. As you drive through town you can see a scene from the Wizard of Oz, James and the Giant Pumpkin, Humpty Dumpty, a church choir and even a hot air balloon. The scarecrows will be on display all around Chester through Oct. 31.

Whether you’re from Chester, or you’re simply visiting this Halloween Season, there are plenty of festive fun to enjoy this Halloween Season. If you’re looking for a day of family fun in a pumpkin patch, or spending the evening Haunt hunting with friends is more your speed, Chester has plenty of exciting Autumn activities to enjoy this October. Halloween comes around but once a year, so if you’re passing through Chester this Fall, make sure to not miss out on the thrills, chills, and scares this year!
Halloween night this year and the influx of visitors it brings to Chester Street, where over the years Trick or Treat has become a must see event. the focus is often on Chester Street, because for many years residents there have been making it a Halloween destination for locals and out-of-towners alike.

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